p-Fluoronitrobenzene → 1,3-Dimethoxy-5-(4-nitrophenylsulphanyl)-benzene

HRID 1603609Notes

Reaction equation

HRID 1603609 reaction equation
[K].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([SH:12])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>CN1CCCC1=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([S:12][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 700027563,5-Dimethoxythiophenol potassium salt

Product 1

HCID 196055141,3-Dimethoxy-5-(4-nitrophenylsulphanyl)-benzeneYield 60.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

0.30 g (0.00144 mol) of 3,5-dimethoxythiophenol potassium salt was dissolved in 5 ml of 1-methyl-2-pyrrolidone, treated with 0.21 g (0.00144 mol) of 1-fluoro-4-nitrobenzene and a spatula tip of Cu powder and stirred at 160° C. for about 3 hrs. Thereafter, the solvent was removed by distillation, the residue was partitioned in water/ethyl acetate and the organic phase was washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:7. There was obtained 0.255 g (60%) of 1,3-dimethoxy-5-(4-nitrophenylsulphanyl)-benzene as yellow crystals; m.p.: 63-65° C.

Workup

  1. customThereafter, the solvent was removed by distillation
  2. customthe residue was partitioned in water/ethyl acetate
  3. washthe organic phase was washed with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane 1:7

Sources & evidence

ORD record
ord-d7038eb4bce54047a6eed820e62a36f6
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…